Substituted 4-(n-sulphoalkylene-aminosulphonyl)-phenyl-azo-phenyl compounds

ABSTRACT

Monoazo dyestuffs which in the form of the free acid correspond to the general formula   IN WHICH X signifies a straight-chained or branched alkylene radical with 2 to 4 carbon atoms, R1 signifies hydrogen or alkyl, R2 signifies hydrogen, chlorine, alkyl or acylamino, R3 signifies hydrogen or alkyl and R4 signifies alkyl, IT BEING POSSIBLE FOR THE NUCLEI A and B to possess further nonionic substituents, AS WELL AS THEIR USE FOR DYEING NATURAL AND SYNTHETIC FIBRE MATERIALS, ESPECIALLY FOR DYEING POLYAMIDE FIBRES. Dyeings obtained yield very good fastness to light.

United States Patent [191 Siegel 1 Dec. 3, 1974 [73] Assignee: Bayer Aktiengesellschaft Leverkusen, Germany 22 Filed: Jan. 14, 1972 21 Appl. No; 217,961

[30] I Foreign Application Priority Data Jan. 15, 1971 Germany 2101685 [52] U.S. Cl 260/205, 260/206, 260/207, 260/207.1, 260/2075, 260/510 [51] Int. Cl C09b 29/08 [58] Field of Search 260/205, 206, 207, 207.1, 260/207.5

[56] References Cited UNITED STATES PATENTS 2,694,727 11/1954 Cross et a1 260/208 X FOREIGN PATENTS OR APPLICATIONS 482.342 3/1938 Great Britain 260/184 723,090 6/1942 Germany 260/205 OTHER PUBLICATIONS Colour Index, 2nd Ed, Vol. 111, pg. 3039, C.l.13030.

Primary E.\'aminerLorraine A. Weinberger Assistant ExaminerC. F. Warren Attorney, Agent, or FirmPlumley & Tyner 5 7 ABSTRACT Monoazo dyestuffs which in the form of the free acid correspond to the general formula HO S-X in which X signifies a straight-chained or branched a1 kylene radical with 2 to 4 carbon atoms,

R signifies hydrogen or alkyl,

R signifies hydrogen, chlorine, alkyl or acylamino,

R signifies hydrogen or alkyl and R signifies alkyl,

it being possible for the nuclei A and B to possess further non-ionic substituents,

as well as their use for dyeing natural and synthetic fibre materials, especially for dyeing polyamide fibres. Dyeings obtained yield very good fastness to light.

8 Claims, No Drawings SUBSTITUTED 4-(N-SULPHOALKYLENE&AMINOSULPHONYL)- PHENYL-AZO-PHENYL COMPOUNDS The present invention relates to new and valuable monoazo dyestuffs which in the form of the free acid correspond to the general formula and also to their production and use for dyeing synthetic fibre materials, especially those consisting of with l to 4 carbon atoms, acyloxy, halogen, especially Cl and Br, carbalkoxy with preferably 1 to 4 carbon atoms in the alkoxy group or by possibly furthersubstituted phenyl.

Lower alkyl radicals or alkoxy radicals are to be understood to mean those with l to 4 carbon atoms.

Preferred alkyl radicals R and R are those with l to 4 carbon atoms. By way of example the following radicals are mentioned:

Acylamino groups are to be understood to mean particularly formylamino, alkylcarbonylamino, phenylcarbonylamino, alkylsulphonylamino and phenylsulphonylamino groups, it being possible for the alkyl and phenyl radicals to be further substituted and the alkyl radicals preferably possess from 1 to 4 carbon atoms.

Suitable acylamino groups are, for example, formylamino, acetylamino, propionylamino, B-chloropropionylamino, butyrylamino, methylsulphonylamino,

phenylsulphonylamino, hydroxyacetylamino, phenoxyacetylamino, benzoylamino, p-chlorobenzoylamino, 2,S-dichlorobenzoylamino, phena'cetylamino radicals.

As acyloxy groups special mention is made of alkylcarbonyloxy and alkoxycarbonyloxy radicals with l to 4 carbon atoms in the alkyl or alkoxy radical.

The alkylene radicals X can also have further substituents, especially hydroxy groups.

Suitable alkylene radicals X are, for example, -CH- 2 2,

3 HO5S-X--NH-O2S- -N N- -N/ 25 v \R Suitable alkyl radicals R and R are particularly those with l to 4 carbon atoms, such as CH C H in which R R R A and X have the meanings given in formula (I), especially those of the formula (III) in which X and A have the meaning given above,

R signifies hydrogen or methyl and R and R signify ethyl, n-propyl or benzyl.

The new dyestuffs are obtained by diazotising 4- aminobenzenesulphonamides of the general formula HO S-X-N-O B- -NH in which X is a straight-chained or branched alkylene radical with 2 to 4 carbon atoms,

R, signifies hydrogen or an alkyl radical and the nucleus A can possess non-ionic substituents, and is combined with coupling components of the general formula in which R signifies hydrogen, chlorine, an alkyl group or an acylamino group, R signifies hydrogen or alkyl and R signifies alkyl and the nucleus B can also have nonionic substituents.

The diazo components of the general formula (IV) are obtained by amidating 4-acetylaminobenzenesulphochlorides or 4-nitrobenzenesulphochlorides with amines of the formula CH OH in which X and R, have the meanings given above, and the acetyl group is converted by saponification or the nitro group is converted by reduction into the amino group. Suitable 4-aminobenzenesulphonamides of the formula (lV) are for example:

l-amino-4-(N-B-sulphoethyl)-aminosulphonylbenzene l-amin0-4-(N-B-sulphoethyl-N-methyl )-aminosulphonylbenzene l O 1-amino-2-chloro-4-( N- B-sulphoethyl )-aminosulphonylbenzene l-amino-2-chloro-4-( N-B-sulphoethyl-N-methyl aminosulphonylbenzene 1-amino-3-chloro-4-(N-B-sulphoethyl)-aminosulphonylbenzene l-amino-3-chloro-4-(N-B-sulphoethyl-N-methyl aminosulphonylbenzene 1-amino 2,5-dichloro-4-(N-B-sulphoethyl)- aminosulphonylbenzene l-amino-2,5-dichloro-4-(N-B-sulphoethyl-N- methyl)-aminosulphonylbenzene l-amino-2,6-dichloro-4-(N-B-sulphoethyl)aminosulphonylbenzene l-amino-2,6-dichloro-4-( N-B-sulphoethyl-N- 2 5 methyl )-aminosulphonylbenzene 1-amino-2-methyl-3-(N-B-sulphoethyl)-aminosulphonylbenzene l-amino-2-methyl-4-( N-B-sulphoethyl-N-methyl aminosulphonylbenzene 3Q l-amino-2,S-dichloro-4-(N-fi-sulphoethyl-N-ethyl)- aminosulphonylbenzene 1-amino-2,5-dichloro-4-(N-y-sulphopropyl)- aminosulphonylbenzene l-amino-2,5-dichloro-4-[N-3 -sulpho-n-butyl-( l -HO S-CH aminosulphonylbenzene l-amino-2,5-dichloro-4-[N-4-sulpho-n-butyl-( 1)]- aminosulphonylbenzene Suitable coupling components of the formula (V) are, for example,

N,N-diethylaniline, N,N-dipropylaniline, hLN-diethyl-m-toluidine, M-B-cy anethylaniline, N-ethyl-N-B- cyanethylaniline,

N-ethyl-N-B-cyanethyl-m-toluidine, N-ethyl-N-B- hydroxyethylaniline, N-ethyl-n-B-hydroxyethyl-m- 4 toluidine, N-ethyl-N-benzylaniline, N-ethyl-mtolyl-benzylamine, N-ethyl-N-,8 phenylethylaniline, N-ethyl-N-B-phenylethyl-m-toluidine,

N-ethyl-N-B-acetoXyethyl-aniline, N-ethyl-N-B- acetoxyethyl-m-toluidine, N,N-di-B-acetoxyethylaniline, N-ethyl-N-B-methoxyethyl-aniline, N,N-di- B-methoxyethyl aniline, N-ethyl-B-methoxycarbonylethyl-aniline, N-ethyl-N-B-chloroethylaniline,

N-ethyl-N-B-methoxycarbonyloxy-ethyl-aniline, N,-

N-diethyl-m-acetylamino-aniline.

The dyestuffs according to the invention are suitable for dyeing natural and synthetic fibre materials, especially for dyeing polyamide fibres into level, rich, orange to red shades with very good fastness to light. They are already absorbed very well on to polyamide fibres in the neutral to weakly acid dye bath. Polyamide fibres are to be understood particularly to mean those of synthetic polyamides such as e-polycaprolactam or condensation products of adipic acid and hexamethylenediamine.

EXAMPLE 1 is filtered off with suction and dried. It dyes polyamide fibres and polyamide fabrics from a weakly acid or neutral bath to give a bluish red with very good fastness to light.

If one proceeds as shown in Example 1, but uses as the diazo component the compounds shown in Column I and as coupling component the compounds shown in column 11, one also obtains valuable water-soluble diazo dyestuffs which dye polyamide orange to bluish red light-fast shades.

17 18 I claim: R is ethyl or propyl; and l. Monoazo dyestuff, which in the form of a free acid, R is ethyl, propyl or benzyl. has the formula I 3. Monoazo dyestuff of the formula:

Cl v R5 HOS-X-N-OS N=N N in which X is alkylene with 2 to 4 carbon atoms; 4- Monoazo dyestuff of the formula:

' l czHa HO S-CH2CH2HNO2S CII2 1 cm 1 and 2 are y g or y 5. Monoazo dyestuff of the formula:

uoas-om-om-mwogs I C2H5 C1 CH3 R is methyl, ethyl or propyl; and 35 6. Monoazo dyestuff of the formula:

01 H3O /C2I'I5 l[03SCHzCH2-I IO2S N:NN\

R is methyl, ethyl, propyl or benzyl. 7. Monoazo dyestuff of the formula:

| 2 5 HOaS-CH2OH2CH2NHOzS-N=NN 2. Monoazo dyestuff of claim 1, which in the form of the free acid, has the formula 8. Monoazo dyestuff of the formula:

.I v c R Q /C2H5 ll()3SClI1-ClI; -CIl2-C1I-;HNO2S N=N-.N\

in which R is hydrogen or methyl; 

1. MONOAZO DYESTUFF, WHICH IN THE FORM OF A FREE ACID, HAS THE FORMULA
 2. Monoazo dyestuff of claim 1, which in the form of the free acid, has the formula
 3. Monoazo dyestuff of the formula:
 4. Monoazo dyestuff of the formula:
 5. Monoazo dyestuff of the formula:
 6. Monoazo dyestuff of the formula:
 7. Monoazo dyestuff of the formula:
 8. Monoazo dyestuff of the formula: 